


What I Want Most

by smolandgrumpy



Category: Supernatural
Genre: Ass Play, Butt Plugs, Daddy Kink, Dirty Talk, F/M, Office Sex, One-Night Stand to Enemies to Lovers (Is that a trope?), Oral Sex, Porn With Plot, Porn with Feelings, Praise Kink, Public Sex, Rough Oral Sex, Rough Sex, Teasing, dom!Dean, public fingering
Language: English
Status: Completed
Published: 2021-01-13
Updated: 2021-02-17
Packaged: 2021-03-15 12:08:01
Rating: Explicit
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 6
Words: 20,328
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/28688409
Author URL: https://archiveofourown.org/users/smolandgrumpy/pseuds/smolandgrumpy
Summary: Dean’s life has been all work and no play lately. When Gabe, his friend, coerced him into tagging along to a club, he couldn’t say no as Gabe has been pestering him for a while now. What Dean didn’t expect was that he’d meet his match in that club in the form of a stunning woman with underlying daddy issues.
Relationships: Dean Winchester/Reader, Dean Winchester/You
Comments: 30
Kudos: 93





	1. One

**Author's Note:**

> What started as a one shot of something I wanted to write for daddy kink ended up a mini series. Apparently, I can't write pwp anymore. Please enjoy.

“C’mon, man!” Gabe urges, his hand comes up to pat Dean’s padded shoulder. 

He’s still in his suit, having gone into work because of that damn project. The deadline is on Monday, and that’s also the day that the execs want to talk to him. He still doesn’t know what’s it about, fears the worst. Maybe he has a reason to? Dean doesn’t know why they would fire him, though. Since he had the news that they wanted to talk to him on Monday, he’s been working harder, knelt himself deeper into the workload, was barely home and if he did, it was just to sleep, only to get up and go to work before dawn. 

It’s crazy. It really is, because it’s not even his dream job but he still  _ needs  _ it. At least until Sam moves over here in a couple of weeks. So, the goal is to hold on to this job for as long as Dean can.

Gabe has picked him up from work, complaining that Dean hasn’t got any time for drinks anymore. Little does Gabe know that he’s been drinking himself to sleep every night lately. And Gabe’s fucking persistent. He was waiting outside the building until Dean had come out and now he coerced him into standing in line for a hip club that has the reputation for debauchery and illegality. It’s just a rumor. Dean’s never been here, but Gabe apparently had.

“This better be good, Gabe,” Dean grits his teeth. The wind is chilly tonight, but for most of the people in the queue, especially women, there's apparently no reason to wear more clothes. 

“It will be, once we get in,” His friend says and rights his suit. It’s weird to see Gabe in a suit, a rare sight, but he wore it because suits always get you into things in the city, “There’s going to be so many girls, huh?” Gabe elbows him in the ribs, “Maybe you can find one to help you to unwind,”

They’re next in line and Dean moves up with Gabe, his hands in his pocket as he shrugs. Well, Gabe is not really wrong. It has been a while since he scored, even longer when he had something steady. It’s not that Dean didn’t want to. It’s more like he can’t find the time. His last relationship, or what felt like it, was over a year ago, and already then, she ghosted him because Dean ghosted her first. Not deliberately, though, he was just busy. And business is a constant lately.

Maybe Gabe is right, Dean wouldn’t mind finding someone tonight. It would be welcoming to take off the edge, forget the looming Monday for a couple of hours. 

They are finally at the front of the queue, and the doorman ushers them through the open door. As soon as they enter the building, the bass of the music hits him. The bass vibrates through his body, traveling up his spine. 

There are plenty of girls, scantily clad, dancing and laughing, waiting for someone to pick them up and buy them a drink. He wonders if he’ll find one he likes. He’s picky, doesn’t want to hook up for the sake of hooking up, if that makes sense. Dean kind of hopes he’d find one with a buried daddy issue, which is really not hard to find in the city, he just needs to be alert and read their body language.

He follows Gabe across the dance floor as the man shoulders his way through to the bar, finds a spot and plants himself there at the counter, making himself bigger than he really is. Dean joins him, smirks proudly at his friend as he orders them a drink. It’s him paying, like he always does with Gabe. Gabe is a good friend but Dean still earns more so that’s the least he can do for what Gabe’s doing for him, being there whenever Dean needs a friend.

While they wait for their drinks, Gabe looks around, eyes scanning the dance floor. Dean watches him at first, watches him smile at something, and turns his head to look at the source that produces the smile on Gabe’s face. 

That little shit has already found his prey. 

“Don’t wait up for me, I guess.” Gabe looks back to Dean and takes his drink, walks across the dance floor to dance with a girl who’s more than willing to share the drink with Gabe. 

Dean turns back to the bar, his elbows braced on the counter as she shakes his head and chuckles. 

Suddenly, there’s a voice beside him and it seems like it’s talking to him.

“Hey, big guy, can you move a little?”

He tilts his head to look at the woman, who appears to be alone. Dean’s interest is piqued. 

“Sure, sweetheart,” He moves a couple of inches to the left, gives her room to press herself against the counter. 

She smiles, leans herself over the top to talk to the tender, her tits squashed on the bar top. While the bartender prepares her drink, she’s still leaning over the counter but she turns to him with a smile. With the tilt of her head and body, he can see that her tits almost spill out. Dean can’t look away even if he wanted to.

“You come here often?” He asks with a crooked smile. 

“Nah,” She smiles back, “I just moved here today, starting a new job on Monday. Just needed a break from unpacking so a friend brought me here. You?”

“First time,” Dean replies, “Where’s your friend?”

“She went to the back,” She says, “Apparently there are rooms?”

Dean shrugs, “I wouldn’t know.” With his next breath, he adds, “Names Dean, by the way.”

“Nice to meet you, Dean, I’m Y/N,”

When her drink arrives, a seat at the bar becomes available and Dean urges her to sit down. She does, albeit reluctantly. While she sits, her skirt rides up a little, exposing the tender flesh of her thighs. He’d like to touch, he really does, but Dean has to be clever about it. 

They are talking while Dean orders more drinks.

“What about your parents?” He asks after a while of talking. He knows that she’s been living in another city, works in the same field as he does, came here for a job but when Dean asked where she’s working, she wouldn’t say and that’s a good girl because people can’t be trusted, not even him. She just finished talking about her one sibling whom she doesn’t talk to anymore. It’s different for him and Sammy. 

“Just my mom, I never knew my dad,”

_ Yahtzee. _

They keep on talking and Dean gets bolder, stands beside her at first with an arm around her waist. He rubs circles on her back with his thumb and she smiles at him, laughs at his stupid jokes too. 

After one more drink, she’s scrambling out of her seat and stands back at the bar, and he should be wondering why but he isn’t. He just knows. She presses her body against the counter and Dean cages her in from behind, lowers his mouth to her ear, places a soft kiss there that makes her shudder noticeably. He chuckles low. 

“You wanna come back to mine?” He whispers lower than he chuckled out before, noses behind her ear and moves lower, plants little kisses down her neck, making her arch her back, driving her sweet ass against his crotch. He’s semi-hard from thinking of what he’ll do to her, only getting harder with the rubbing. 

“You want that?”

“Yeah,” Dean darts out his tongue, swirls it around her earlobe and there’s an actual moan. 

His right hand travels down the front of her body, fingers span wide on her stomach and it dips lower. He watches her breath hitch in her throat, feels her shivering. 

“What would you do to me, huh?” 

Instead of answering right away, Dean’s hand goes further down, hitches the seam of her skirt up a little, teases the tip of his middle finger along her clothed pussy. 

“Oh god,” She groans and throws her head back to rest on his chest while her back is still arched. 

He chuckles, “Call me Dean,”

His hand goes further down, and she parts her legs a little. A fucking good girl, indeed. He rubs long her lace panties, feels the fabric damp. He gets bolder too, his fingers hook into the crotch of her panties, pulling it aside. 

It’s skin on skin and Dean lets out an audible groan at the wetness he feels, bites into the junction of her shoulder where it meets her neck. It prompts her to drive her ass into him harder. 

“You’re fucking soaked, baby, is that because of me, huh?”

He flicks at her clit with his thumb, dips just inside of her wet pussy with the tip of his middle finger. 

“Uh-huh,”

“Yeah?”

“Yeah,”

Dean chuckles as he pushes his finger in some more but not too much. It’s just a tease after all. He closes his eyes, groans again. He’s fucking hard by now and he presses closer to her ass, making her feel what’s going to await her.

“You’re so wet and warm,” He breathes out next to her ear, “Who’s making you so wet, huh?” 

“Fuck,” 

“Who, baby?” He goes further in, applies more pressure with his thumb.

“Y-you… you, daddy,”

Y/N doesn’t seem to have noticed the word she let slip out, or she’s too far gone to care if he’d be appalled by it.

He sucks in her earlobe with a chuckle, releases it before he nibbles at them. Not so much that it hurts, but enough to inflict a little pained pleasure, “Yeah? Did daddy make you all wet, huh? Jesus, you’re so tight and warm, making me want to fuck you so bad,”

“Do it,” She drives her ass back, wriggles with it deliberately, “Please? Daddy?”

_ Jesus fucking Christ.  _

She really is into this. 

“Gonna take you home first, baby, you up for that? Huh?” His other hand massages up her throat and Dean paints along her mouth with two of his fingers. He can’t really see but he can feel. 

Nodding her head, she opens her mouth, sucks his digits in, and swirls her tongue around them. 

_ Fuck. _

“Your mouth, baby,” He whispers, “Feels good around my fingers, would love to see them around daddy’s cock,” 

“Mmmh,” A moan of approval accompanied by a shiver.

“Would you like that, huh? Like for daddy to use your mouth? Let you suck my cock like the good girl you are?” Her pussy clenches around the one digit and Dean grins, “Yeah you do. Gonna use your sweet mouth, can’t wait to feel those lips around my fat cock, baby girl,” He pushes his fingers deeper into her mouth, feeling her retching against him, “Yeah, gonna make you choke on daddy’s cock. That’s what you like, don’t you?” 

She hums around his digit, and her pussy clenches some more. 

Dean really hit the jackpot tonight. He should send Gabe a thank you card for bringing him out here.

“C’mon, let daddy take you home,” 

  
  
  


_________________________________________________________

  
  
  


Y/N didn’t realize the word that slipped out of her mouth, but she was glad Dean ran along with it. Using it even more afterward too. He got harder hearing it out of her mouth, an added bonus, really. There aren’t a lot of guys who are into it and god, that guy is hot and is fully on board with it? She fucking loves this city. 

He doesn’t live too far, it was just a ten minute ride, where he moved close to her and let her drape a leg over his thighs. His fingers are in her pussy, fucking her with them while he fucks her mouth with his tongue to the same rhythm. Her hand is on his crotch, palming and rubbing him through his slacks. 

Dean groans into her mouth, parts just for a minute to catch his breath, and whispers low, “Jesus, can’t wait to get my dick into that tight pussy, baby girl,”

_ Fuck _ . She can’t wait either. His filthy mouth turns her on so much. 

The cab comes to a halt at a building which is in the nicer part of the city. She wished she had enough money to live here one day. Maybe she will one day with the new job she’s starting on Monday. 

He lets go of her long enough to pay the driver and she tugs her skirt down as she gets out. Dean holds out a hand for her to take before he guides her into the building and into the elevator. 

Pushing her against the wall, he presses his one thigh between her legs, the skirt riding up in the process. He kisses her again, his one hand braced on the elevator wall, his other hand around her throat, applying enough pressure for her to not feel like he’s restricting her. His mouth hovers around hers and he moves in, pecks her lips gently, “Come on, rub your sweet cunt on my thigh, baby. Get yourself warm and nice for me,”

She nods and he claims her mouth, kisses her hard, the scruff rubbing against her cheek, his tongue licking into it deep as she moves her hips and rubs her ruined panties over his clothed thigh.

_ God _ , the friction feels phenomenal. 

The elevator pings, and Dean chuckles as he pushes himself from her, chuckles, because she’s still rutting against nothing. 

“Fuck, you’re really something,” He whispers as he manhandles her out of the elevator only to drag her along the hallway.

It’s easy, she thinks, so easy for him to manhandle her around. He’s so broad and strong and just...  _ fuck _ , she wants him so bad. 

He comes to a halt in front of a door that says  _ 823 _ , reaches into his pocket to pull out a set of keys and she stands behind him, reaching her arms around his body. Her one hand palms over a clothed, yet still so fucking hard cock, while her other hand tries to unto his belt buckle. 

“Baby,” Dean chuckles, “Can’t open the door when you’re distracting me,”

“Just want you so bad,” She says, her forehead leans against his back and she feels his muscle shifting. 

Y/N got the belt loose before Dean found the keyhole, her hand sneaking into his pants, traveling over the tuft of pubic hair until she wraps her fist around his dick. 

He lets out a groan and closes his eyes for a moment before he goes on with trying to get into the apartment. 

Dean shakes his head, “You really want that dick, huh?” 

“Yeah,” She whispers against his back, her hand now jerking him off. She squeezes a little more at the head of his dick, and pads over his slit to smear the precum around his tip. 

“Fuck, baby girl,” Dean mutters under his breath and she hears a click before he turns around, making her release her grip around his cock. 

He crashes his mouth on hers, kisses her hard, his fingers fisting in the hair at the back of her head as he pulls her into the apartment with their lips still attached. He kicks the door closed with one foot. 

After a while of intense kissing, Dean pushes her away, making her stagger back. 

“Strip, baby,” He says in an absolutely dirty voice all deep and husky and she does because god, she would be damned if she didn’t want to be his good girl tonight. 

Her shoes are off quick and she pushes her skirt down, her underwear comes right after before she pulls her top over her head.

Dean has released his cock, is fisting it while he watches her undress herself in front of him, groans when he sees her nakedness. 

“Beautiful,” He lets out, smirking a little. It’s a boyish grin and that’s when he slips out of his role a little, she thinks. With his next breath, he catches himself again.

Normally she’s pretty self-conscious, but she has the feeling that the guy standing before her who’s ready to get his cock wet, doesn’t mind how she looks since they came this far already. Plus, the light’s still off, but the light from the moon and skyscrapers shines in, making her see enough to want him even more.

His dick is heavy and hard in his fist, as he massages it up and down. Her mouth waters at the sight.

“Get down on your knees,” 

_ God _ , yes. 

Finally.

Y/N kneels before him and Dean takes a step further in as he groans. Her mouth is already open and inviting, but he takes his time, rubs his heavy dick over her face. 

“Looking so good for daddy, baby,” He huffs out. 

The rubbing smears his precum on her face. She feels wet drops here and there and the scent of his arousal is intoxicating. God, it’s making her drool. 

“You want my dick, huh?” He asks, tapping his dick lightly to her cheek, “Want to show me how good you suck cock?”

“God, yes,” She agrees with a frantic nod of her head.

“Call me daddy, baby,” Dean chuckles, “Open up your mouth wider, stick out your tongue,”

She does what she’s told.

“Good girl. That’s daddy’s good girl,” He says almost fondly and slaps his dick against her awaiting tongue, “Now suck,”

Well, she doesn’t need to be told twice. Sealing her lips around the head, she starts to suckle at it and Dean groans, throws his head back as she looks up.

“That’s right,” He whispers as soon as he catches himself, “Look up at me, I want to see how much you like sucking my cock, baby,”

She tries her best, she really does. His cock is thick, the taste of precum and a day’s worth of musk is heavy on her tongue, the scent penetrating her nose. It makes her suck him harder, makes her leak profoundly between her legs because she just wants him so fucking much.

“Spread your legs, touch yourself,” Dean mumbles, “I wanna see you touching yourself, baby. Wanna see you make yourself come while you suck my cock,”

_ Oh god, yes _ . She’s so close too. It’s no wonder, as she’s been balancing on that fucking edge since he fingered her in the club. 

Spreading her leg but still on her knees, she pushes a hand in between, fingers herself, and rubs against her clit. The sound of her wetness is loud in the room. Dean groans when he hears it.

“So fucking good, baby girl,” He huffs out. His hand comes to push a strand of hair out of her face to see her better, “Sucking daddy’s cock so well,”

“Mmmh,” She hums in approval with his dick in her mouth and fuck, hearing him praise her just does things to her and she comes, quick, hard, humming and shrieking with his cock in her mouth. It makes him push his pelvis against her harder, making her choke when the tip of his dick hits her throat.

“Good girl,” Dean hums as he pulls his dick back but he leaves her to suckle at his tip, “Such a good girl for daddy, I’m so proud,” His hand finds the side of her face, applies pressure on his palms as he grips it, “I’m going go fuck your face, okay? Can you take that, huh? Take my dick?”

She looks up and hums, nodding her head.

He smiles down fondly, his teeth showing white and the crinkles around his eyes run deep. His grip around her face tightens a bit as he starts to fuck into her mouth, getting deeper inside with every thrust and she braces her hands on his thighs, fingers gripping at the fabric of his pants when she feels his dick choking her. 

Dean presses his pelvis to her face, his pubic hair tickles her nose and he stays there for a while until she taps at his thigh because she feels like she’s going to pass out if he doesn’t let her come up for air. 

And it’s weird. Really weird. She should be scared of doing this with a stranger, yet she trusts him. He has won her trust in such a short span of time. Some would call it naivety. 

When he releases her face, she gulps for hair, trying to fill her lungs before he thrusts in again and he does. He gets faster too. The drool is running down her throat, her chest is wet. 

“Fuck,” Dean whispers between thrusts, “Your mouth is fucking perfect, baby. You taking my cock so well,” 

It makes her wetter hearing it and she’s sure that there’s a pool of her juice right below her. 

“You want my come, baby? Want me to come in your mouth?” 

_ Oh, god _ . More than anything right now. 

She wants to feel him, to fucking taste him, so she nods her head as he stops his thrusts for a second. 

Dean grins cockily. It’s really a good look on him, “Take it all, okay? But don’t swallow yet. Keep it in your mouth, baby,”

Another nod. 

“Jesus,” He groans as he picks up his thrusting, “You’re perfect, baby girl, so good for daddy,” 

His thrusts are faster before he comes and when he does, he lets out a deep growl as he pulls his cock out and fills her mouth with his cum. 

Y/N does as she was told. She doesn’t swallow, instead, she opens her mouth, letting him pour in every drop he can milk out of that beautiful cock of his. 

Dean’s spent dick is getting softer, but it still looks impressive, at least when it dangles so close to her face. 

There’s a drop of cum on the corner of her mouth and he scoops it up with his thumb, pushing it into her mouth. His eyes are on her, a glow around him after his release. It makes him even more attractive and she wonders how fate is sometimes cruel to give her something she craves but takes it away again because it’s a one night stand. That’s all there is. He knows it as much as she does.

His other hand goes up below her eyes, brushes away the smeared mascara and with his thumb still in her mouth he tries to angle his stance to get her other eye as well. 

Her mouth is full of cum and drool, almost spilling over but Dean takes his time, stands back to marvel at her. 

“You look so pretty,” He says, again with a fond undertone, “Would take a picture if I could,” The cum’s floating over, and Dean pushes his thumb inside her mouth some more, “You may swallow now, baby,”

She does, closes her eyes to get the thickness of his cum down with his thumb still in her mouth. She sucks at the digit, signaling to him that it’s all gone.

“Open up,” He whispers, “Show me,”

Y/N smiles when she does, opens her mouth wide to show him that she’s swallowed it all.

He chuckles, “Good girl, you’re really a good fucking girl, baby,” 

Taking his thumb out, he brushes it along her lips before he grabs at her arm and pulls her up. He kisses her then, letting out a languished groan when he tastes himself on her tongue. 

“Down the hallway, the room to the left. I want you spread out on my bed, play with yourself okay?” 

Dean kisses her on her nose and she nods before she makes her way to his bedroom. Climbing on his bed, she positions herself with her back against the headboard and spreads her legs. Her one hand plays with her pussy, fingers dipping in deep, before rubbing at her clit wetly. She closes her eyes, thinks about what just happened. Thinks about his voice that she’ll probably never forget. Thinks about his taste that she won’t be able to erase out of her mind. 

It’s not long before Dean joins her, in one hand bottled water, in the other are her clothes and shoes. He’s really being considerate. Or he’s a neat freak. Either or. Not that it matters.

He drapes her clothes over a chair next to the bed, sets her shoes right below it before he unscrews the water and hands it over to her to drink. The coldness of it travels down her throat, making her shiver. Maybe she shivers of anticipation too, who knows. 

Setting the water on the nightstand, Dean continues to undress, taking off his suit jacket and drapes it over another chair. While doing it, his eyes are on her. 

She’s still rubbing herself, fondles her tits one-handed too, pinching her nipple, and arches her back.

“That’s it,” Dean croons, “Touch yourself, but don’t make yourself come, I wanna feel you come on daddy’s cock,” 

_ Oh god. _

She wants that too.

He watches her some more as his fingers slowly unbutton his shirt. Too slowly and it’s not fair because she just knows that he’s teasing her. When he takes his shirt off, she can see how broad he is, can see the muscles moving. He’s soft and firm and so fucking delicious. By the time Dean takes off his underwear, his dick is already more than semi hard. It’s impressive, really. She still can’t believe that she had that down her throat.

When he’s naked before her, he tugs at his cock, jerks it while his eyes are on her and he walks closer, climbing on the bed and walks closer to where she is on his knees. 

“Jesus,” He growls, “You’re making me hard again, baby,” 

There’s a smile tugging at her lips as a sense of pride washes over her. 

“Will you fuck me now, daddy?” She says it in her best sultry voice.

“No,”

“No?” She frowns a little.

Dean chuckles, “No, I gotta taste you first,” He shoulders himself between her thighs, “Be a good girl, hold your legs up for daddy,”

Shamelessly, she hooks her arms around the back of her knee as she pulls them up and apart, almost folding herself in half. That’s how eager she is to spread for him. 

His big hands are on the back of her thighs, helping push her back as he hovers above her wet pussy, “That’s my good girl,” He chuckles, warm air hitting her core, and she trembles.

He doesn’t stall, instead, he buries his face right in there, sucking and lapping around her sensitive nub like it’s the only thing that keeps him the fuck alive. 

“Your cunt’s so sweet, baby,” He moans, as he spreads kisses all over her pussy, “Could eat you for days,”

Alternatively, he switches from sucking to lapping, and her hand finds his hair fingers, pulling at it, but Dean doesn’t seem to mind. He even starts to hum and that drives her fucking crazy.

It’s when he pushes in a thick finger that she almost loses it. Has to throw her head back and close her eyes when he curves the finger just right. He soon uses another finger, rubbing against her inner wall with it while he sucks at her clit and she just knows. She just fucking knows that she’s going to come again.

Her grip tightens in his hair, fingers digging into his scalp but Dean goes on, licking her and sucking her while he thrusts his fingers inside of her.

“Da- fuck- daddy,” She bites on her lip and the wave that hits her is strong, making her release her own legs, making her squeeze them around Dean’s head, “Fuck, oh my god,”

Dean chuckles as he spreads kitten licks on her clit. He pulls his fingers out and they pop out with a wet squelching sound, “You’re doing so good for me, baby, but please, call me daddy,”

The way he looks up from between her legs makes her heart race faster. Half of his face is drenched with her slick and there’s a glisten in his eyes while his lips are crooked into a smile that’s full of bravado.

He’s still fingering her lazily, circling his thumb soothingly around her clit, not applying too much pressure because he knows that she’s sensitive. Dean leans down and kisses her, swirls his tongue around her own. He parts with a bite on her lip, making her squeal and laugh. 

“Can you fuck me now, daddy? Please?” She pouts a little for the effect but god, she’s so desperate for his cock. Desperate to feel him inside of her. 

“I can’t believe I’m saying this and you can say no, okay?” He starts while he lays himself next to her, kissing the side of her face while he rubs between her legs. Dean dips down sucking a nipple into his mouth, bites on that too, chuckles when she moans.

“What?” She asks, fearing the worst. Fearing that he’ll say that it’s been a mistake and he only wanted to go this far and no further, fearing that maybe he’ll say that he’s too tired, or that he wants to put off fucking her for real for another day, or fuck, what does she know? There are so many possibilities that run through her mind right now.

Dean noses along her cheek, his nose is still damp, and she can smell her scent off him, “I was wondering if I could fuck you without condom, and before you say anything, I know it’s stupid but god, you feel so fucking good around my cock and you’re so fucking wet, I really want to feel it,”

_ Oh. _

Y/N can’t believe what she’s going to say either. She’s never been so careless before but fuck, she’s really so far gone, and as she said before, she doesn’t know what it is but she fucking trusts Dean. 

“I can’t believe that I’m saying it either, but please please, fuck me raw, daddy,”

“Jesus,” Dean groans as he quickly captures her mouth, tongue swiveling against her own. He sucks in her tongue before he releases it, “Come on, get on top of me,”

With one swift movement, he manages to manhandle her on top of him and she straddles his body, moving down inch by inch. He groans out again when she feels her leaving her wetness on his body on her way down. 

Spreading herself over his hard cock, she grinds her pussy lips on it, slicks it up with her juice, teasing him in the process. 

“Fuck, baby girl, don’t be a tease now,” 

She chuckles but doesn’t stop and he lets her, probably enjoying the view and her playfulness. When she’s had enough and almost bursts herself, she grabs at his cock and points it upwards. Slowly, oh so slowly, she lets herself down.

Dean let out a groan, bites down on his bottom lip as she works her way further down his shaft. He helps a little, pushing his hips up, and down again when she manages to take all of him. 

Her hands are braced on his chest and he rubs along her thighs. She needs a moment to get used to it, her walls fluttering around his girth.

“Jesus Christ,” Dean mutters under his breath, “You feel so fucking good, baby, like I thought you would. So wet and tight,”

Y/N’s plenty wet, Dean’s right about that and she gets even wetter as she starts to bounce on his shaft.

“So good, baby,” He coos, his hands on her hips, helping her guide herself up and down, “So pretty bouncing on daddy’s cock, fuck,” His one hand goes to her tit, squeezes it tight before he slaps down on her nipple, “That’s it, baby, fuck me,”

And that, she does. His words make her wetter, make her bounce on top of him harder. Up until she’s worn out and retorts to grinding. 

Dean pulls her down by her arms, kisses her as he thrusts his hips up to not lose the rhythm, “Is my baby tired, huh?”

“Uh-huh,” 

“Should daddy take over?”

“Yes, please,”

With a chuckle, Dean turns them both around until he’s on top, without slipping out of her. He gets up on his knees and pulls her closer by her legs so that her ass is on top of his thighs as he begins to fuck her deep and slow.

“Like that, baby?” He asks with one thumb circling her clit.

“Uh-huh,” 

There’s really no coherent word that she could bring past her lips. 

“Yeah?” He asks as he thrusts harder. He changes angles then, puts her down on her back and pushes her legs up so that he can thrust in even harder, “Like it hard?”

“Fuck, yeah,” 

“That’s a good girl, baby,” Dean whispers, “Your cunt, that’s mine tonight, isn’t it?”

His thrust gets deeper, just the way she likes it, making her roll her eyes to the back every time he hits her cervix.

“Yours,” She manages to say, “Fuck,”

“Who am I, baby girl?”

“Shit,” 

He starts to rub her clit while his slows his thrusting, but he still goes in deep, reaches her every corner where she wants him most, “Tell me, I want to hear you say it,”

“Daddy-, fuck, daddy, you’re my daddy,” 

“That’s right, baby girl,” He coos, “I want you to remember that, okay? Remember who makes you feel good,” 

He talks like she could ever forget him. It’s so fucking hard to and she doesn’t think she’d be able to even if she would try.

“Oh my-,” She bites on her tongue, knows that she should say his name, “Daddy, I’m fuck- you’re going to make me come,”

“That's okay, baby, come,” He pants, “I wanna feel you coming on my fat cock, can you do that for daddy, huh?” His one hand goes to her throat, claws around it and squeezes it just right. It gives her the much added trigger to explode.

_ Fuck _ , who taught him to fucking talk like this?

Dean chuckles, “I can already feel your cunt squeezing around me, baby, you’re close, so fucking close, ain’t you? Come now,”

It’s not like she needs permission, they didn’t work that out but fuck, if she’s not a good girl. So she comes, right around his cock. He releases his hand around her throat, brushing over it just lightly to smooth away the pain.

“Jesus, fuck,” Dean groans as her walls squeeze down on him. His movement starts to falter and she can feel that he’s holding himself together, “You feel so good coming on my cock, baby. You just got tighter too, fuck,”

It’s about only three hard thrusts later that he starts to tremble, “Where do you want me to come?” 

She looks up at him, her hands curl around his biceps with every hard hit to her cervix, “I want, fuck, I want you to come inside, daddy, please? Wanna feel your cum running out for days,”

“Baby, you’re a fucking nasty girl, ain’t you? Fuck,” 

Oh god. He’s right because that’s what she fucking is. She has no shame whatsoever. 

“Gonna come so deep in your cunt, baby, mark it as mine,” He thrusts faster but not as deep anymore, “How does that sound?”

“Please,” She is basically begging him.

“That’s my good girl, taking my cock so well and now my girl wants my cum too, fuck, you’re so fucking perfect,” He growls low, and pushes in twice more, hitting her cervix before he stills and spills his cum deep inside of her. 

Dean lets himself fall on top of her, braces his elbows on the side of her face so as to not crush her. He dips his head down, kisses her deep and tender while his dick still twitches inside of her with his release.

  
  
  


_________________________________________________________

  
  
  


They took a shower together after that, cleaning themself off their filth and cum, and Dean’s worn out but he couldn’t help himself, made her come again in the shower on his dick alone with his thumb buried in her ass as he fucked her from behind. If he should fuck her again, he wants to try that back hole too, is almost sure that she’d let him because she went nuts when he stuck his thumb in there. Jesus, he hopes there’ll be a next time. It doesn't happen often that he wants to see a one night stand again, but with her, he’s ready to make an exception.

Now she’s really tired and almost falls asleep in his arms while he carries her over to his bed. Dean tucks her in and slides in next to her, pulling her into him and letting her rest her head on his shoulder. He kisses her gently, hand brushes away the hair from her face, knuckles grazing her cheeks.

He feels her smile into the kiss.

“Thank you,” She whispers and is already drifting off.

Dean chuckles, “You’re really something else, baby,” 

  
  
  


*

  
  


He wakes in the morning, realizes that the bed next to him is empty. Tilting his head around, Dean looks at the chair, sees that her clothes are gone along with her shoes.

Heaving his aching body from the bed, he sits up and rubs his hands over his face, “Fuck,”

She’s gone. Dean doesn’t even have her number. He really doubts he’ll see her again and that’s a fucking shame. 

  
  
  


*

  
  


Monday rolls around and Dean’s nervous. 

He’s pissed too, because he called Gabe and persuaded his friend to go to the club again but of course she wasn’t there. He waited longer than he should have, turned down four girls because he wanted to meet the right one. He had been losing sleep because it had gotten late and the thought of having to be in the office in five hours doesn’t help. 

So he sits in the meeting room, waiting for his bosses to arrive to maybe fire him, even though he fucking aced the presentation to the project this morning.

“Hello Winchester,” Mr. Turner says as he sits down and Mrs. Mills takes the chair next to Mr. Turner. They sit across from him. 

“Mrs. Mills,” He nods, “Mr. Turner,”

“Have you been informed why we called you in today?”

“Not, really no.” Dean shakes his head as he rubs his sweaty hands on his slacks. 

Mrs. Mills smiles, “We are thinking that you’re doing a great job,”

“I am?” He cocks an eyebrow, as if he can’t believe it.

“Yeah,” Mr. Turner chimes in, “The reason for this meeting is this. You know that Mr. Campbell is retiring in a couple of weeks, right?”

“Yeah,” 

Dean knows. He’s been invited to the farewell party organized by Mr. Samuel Campbell himself. 

“Right,” Mrs. Turner nods, “We are considering you for the position.”

“Really?” He can’t hide the grin, and even if it’s a job he absolutely doesn’t want, it feels great to be considered for it.

“There’s a catch, though,” Mrs. Miller says and of course there is. There’s always a catch in this company. 

“We have a newcomer from an external company who also applied for the job. The person has a good reputation and great recommendation letters.” 

Of course. Dean nods. They always have. 

“We want to watch the two of you for about a week, two tops, see how much you’re willing to give of yourself, how driven you both are. We’re going to make a decision and please don’t take it personally if it’s not you. I’m sure the next position that opens up will be glad to have you.”

“Is this a competition?”

“See it as such, yeah. We talked about it in the boardroom and we really think it’s fair to give the other person a chance to get some more work experience in the company before we would consider them suitable for the job. With you, Mr. Winchester, we already know it, but that doesn’t mean that you have the job for sure.”

“Right,” 

He’s never good at losing but that’s because Dean never loses. He’ll have an advantage over that dude. It’s probably going to be a piece of cake. He barely has to lift a finger, probably.

“Are you ready to meet your competition? There are projects you have to work on together, so it would be good if you get acquainted with each other.” Mrs. Mills asks.

“Sure,” Dean shrugs with a nod.

Mrs. Mills gets up from her chair to walk to the door. She opens it and keeps it open wide and then it feels like the air has been punched out of Dean’s lungs.

He’d recognize that face anywhere. He also remembers those long legs in heels.

“Mr. Winchester, meet your new colleague, Ms. Y/N Y/L/N,”


	2. Two

“Please take a seat,” 

Mrs. Mills shows Y/N where she should be sitting, and it’s right next to Dean.

_ Fuck. _

She’s going to be the one competing with him?

This is ridiculous.

And in that moment, Dean just knows that he’s fucked.

He could easily handle another male competitor. Hell, he wouldn’t have any problems with female competitors either because they’re even easier to wrap around his fingers. But her? 

_ Shit. _

Dean wants to rub over his face so bad. Wants to pinch his eyes. Maybe they betray him? Maybe his mind only wants him to see what he really wishes to see.

This is a bad dream right? How is he supposed to be working with and against someone who he knows the taste of? Someone who he knows likes to be fucked hard and swallows his cum like it’s the best fucking thing? Someone who lets him come deep inside so she’d be dripping him for days? 

_ Jesus. _

Dean has to bite down on his bottom lip so as not to make a sound. 

He just imagined her still dripping his cum. He shoved two loads deep inside that sweet cunt. The chances are high that she’s still leaking him.

His dick stirs uncomfortably at the image in his head. It also doesn’t help that he catches a whiff of her perfume when she walks past him. It intoxicates his brain. 

She’s standing there right next to him and it feels so familiar, yet so painful. 

“Mr. Winchester?” 

Her voice penetrates his thoughts, jerks him back to reality and Dean scrambles himself out of his seat to stand up because that’s the correct thing to do, right? Fucking etiquette. If it was up to him he’d had her over his knees and spank the shit out of her for not telling him where her new workplace is.

Y/N’s holding out a hand for him to shake and he takes it, feeling the electric current traveling up his arm as soon as he touches her. 

_ Call me daddy _ , he wants to say, but doesn’t. Instead, he forces out a smile, “Call me, Dean,” 

“Right,” She says with a nod, “Dean. I’m Y/N, nice to meet you.”

“The pleasure’s all mine,” 

That’s something he really means and there’s just a brief moment of eye contact before she looks away, pulling her hand out of his grip. Too soon for his liking but he reacts fast, pulls up the chair for her to sit on. 

“Thank you,” She smiles and Dean can read that. It’s one that says that she’s not entirely sure about Dean’s motives. Not sure if Dean is angry or not. 

He’s not really angry if he thinks about it. At least not at her. At fate maybe, but she hasn’t done anything wrong. 

They sit and listen to what the bosses have to say but Dean couldn’t concentrate. He watches her out of the corner of his eyes. Her business persona is very different from the playful baby girl that came on her daddy’s cock, came on Dean’s cock. But he likes the professionalism of her too. Like, she’s all tough and serious, is a fucking good girl indeed. She’s even taking fucking  _ notes _ !

She’s really in for the win, and Dean wonders if he should tell them that he doesn’t even want the promotion that fucking much. But again, where’s the fun in that, right? Because yeah, it could be fun working with her, against her, over her, under her, buried deep inside of her, even though it would also be pure torture.

Finally, the bosses have stopped talking and disappear with the promise of sending them the schedule of their project support meetings for the weeks ahead.

However, Dean’s heart jumps when he sees her wanting to stand up and leave too, but then Mrs. Mills tells her to stay behind and get acquainted with Dean and he watches her sitting back down in her chair. Yeah, thank you very much for that, Mrs. Mills.

As soon as the bosses have gone, Dean stands up and the pushing back of his chair makes the metal screech along the floor. She squints. 

“Jesus, Y/N!” He hisses as he walks the two steps to stand behind her, “Why didn’t you tell me where you’re going to be working?”

“Well,” She says but she doesn’t look up to him, instead she keeps her eyes trained on her notebook, “In my defense, I didn’t know, okay? I knew that it was a Dean but I didn’t know that it was going to be fucking  _ you _ !” 

He leans down, braces one of his hands on the back of her chair. His other one is on the table while he practically cages her in. From here her scent is even more alluring. It does things to him that he can’t even explain. Partly, it makes him want to eat her up alive.

Dean noses at her hair, inhales deeply, doesn’t care if she thinks he’s a freak because let's be honest here, they’re both fucking nasty and he thinks that they’ve established that. 

“Why did you leave without a word?” He asks in a low voice. 

She goes still, doesn’t even breathe as far as he can tell.

Slowly, she tilts her head around and their noses almost touch. It would be easy, so easy for him to kiss her but he doesn’t. Instead, he stares her down but he wasn’t prepared that she’d stare back. 

_ God _ , she looks absolutely gorgeous. His dick twitches in his pants because his dick fucking  _ remembers _ .

“I didn’t think it was more than a one night stand, Dean,”

“Well, it probably wouldn’t have been if you wouldn’t have left.”

He can’t believe his own words. But it’s the truth. The girls he takes home are never more than a one night stand and yet, he can’t explain why he thinks that she is more than that. Can’t explain why his cock, his body, his mind, his fucking heart wants her so much. He might also sound like he’s hurt and maybe he is. And it’s not even her fault. Dean should have made himself clearer after he tucked her into bed but he was just fucking exhausted and by the way she was too, he thought that she’d sleep longer than he would.

“What would you have done, Dean?” She asks, her voice a whisper because they’re still so close, “I don’t think any good would have come of it if I had I stayed.” 

“I don’t know,” He shakes his head. His mind raced at the question. Yeah, what would he have done?

He grins, “I would have maybe fucked you again, because goddamnit, I can not forget how your sweet cunt clenched around my fat cock,” 

Y/N’s tongue darts out, wets her lips and Dean replicates it. 

“Dean,”

“I just knew that it wasn’t a one time thing for me, okay? I knew right before I fell asleep that I wanted to see you again. There was hope in my fucking heart that I would get to make you come again. I hoped that I would fucking see you again. I fucking  _ hoped  _ that you’d still be there when I woke up, that you would let me treat you right, that you’d fucking let me bring you home, take you out, the whole shebang,”

“It wasn’t just a one night stand for you?”

“No!” He’s still leaning close and smashed his fist on the table, making her flinch, “Jesus Christ! I thought I just said that?”

“You mean you want to carry on with the fling?”

“It’s not just a fl—” He lowers his head, rests his forehead on her shoulder, “God, you know what? Forget it… but yeah, I want to carry on. More than anything,” He mumbles. 

“But—”

“Yeah,” He huffs out, “This is going to be hard,”

“We’re adults, we should be able to work together.” She whispers softly. Too soft, and he can hear it, can hear the longing she has because he feels fucking same.

“Should we?” He asks, just to make sure. Adulting seems to be fucking hard right now.

“Yeah,”

“Goddammit,” Dean curses under his breath, “Do you know how hard it is for me to pretend nothing happened? How hard it is to fucking pretend that I don’t want to bend you over the next surface and fuck you senseless? Do you have  _ any  _ idea how all I want right now is to feel your sweet pussy around my dick again and I had to fucking jerk myself off last night with the image of you on top of me and hearing you call me  _ daddy  _ over and over again?”

“You did?” There’s a small smile tugging at the corner of her lips.

“Yeah,” He frowns, but he chuckles afterward.

“How hard is it?” She asks, raises one eyebrow at him. She looks absolutely cocky.

“Jesus,” Dean growls, and it’s time, he can’t hold himself back anymore. He moves forward, catches her lips. The familiar feeling is there again, the way she presses closer, the way she fucking  _ lets  _ him kiss her. He breaks the kiss only to murmur “So fucking hard, baby girl,” against her lips.

She laughs, and Dean doesn’t really want to part from that sweet fucking mouth, but he knows that he has to. They’re at work for god’s sake. Reluctantly, he pulls himself off her but not before he pulls her bottom lip between his, gives them a little suck and a bite, just to hear her moan against his mouth.

  
  


_________________________________________________________

  
  
  


Somehow, they have managed to agree that it’s work first and play later. It doesn’t help that while the bosses see how she’ll be holding up, they just put another desk into Dean’s office. So now, they are sharing offices too. 

It doesn’t help her sanity, to be honest, but apparently, she’s been holding up better than he does. Dean has been avoiding her since the meeting, doesn’t want to be too close, and she knows the reason why and it’s really amusing to her.

  
  
  


*

  
  
  


In the afternoon, Y/N’s working on a project while Dean was at a meeting and she needed binders from the shelf, so she took off her shoes and rolled her chair to the bookshelf to get to the top one. 

Pulling out one binder, she rifles through it to see if the numbers she needs are in there when Dean walks in.

He was so quick to be by her side, holding her chair for her while balancing his laptop in his other hand and he curses under his breath, “Jesus, Y/N, that’s not fucking safe. Next time take a chair without wheels, okay?”

It’s really cute how he cares, she can’t lie about that. But she wouldn’t be who she is if she didn’t find things to rile him up.

“Yes, daddy,” She whispers with that grin that’s more than mischievous and he groans audibly while he rolls his eyes to the back of his head.

He’s faking annoyance but he’s not letting go of that chair she’s standing on, holding it for her and she thinks he takes the opportunity to look at her ass too because, when she finishes, he turns away, taking wide strides to his desk and maybe she’s wrong but his legs were bowed more than they usually are.

  
  
  


*

  
  
  


It’s only late afternoon now, and she’s working across from him. She’s distracted while she reads over the schedule they just sent her. 

_ Oh god _ . There it is. The warm feeling of something running out of her. 

It’s Dean’s cum.

And even though she cleaned herself thoroughly it still keeps leaking out. Just how much did he come? Seriously. 

“Did you get the schedule?” Dean asks from behind his monitor. 

“Yeah,” She almost squeals because of the warm feeling, and now his cum is pooled in her panties.

“Everything okay?”

“Yeah, yeah,”

Dean gets suspicious, stands up behind his desk to peak over, “You sure?”

“It’s nothing you want to know,” She mumbles, her hands going over the mouse to open up her schedule.

“Why do you think I don’t want to know?” He asks and now he’s walking around his desk to come stand next to her. He’s at least semi-hard because his pants are bulging. She can see it even better when he’s not wearing his suit jacket. Well, to be fair, that thing is hard not to notice. 

“Because,” She states, “It’s not going to help you,” 

“Well, there’s obviously something that makes you feel uncomfortable and if it’s me, I need to know,” 

“Dean, stop!” She groans, “Your cum just leaked out of me, okay? It’s nothing. Are you happy now that you know it?”

He rubs a hand over his face, the scruff sounds loud in the otherwise quiet office, “Jesus, this is torture! I can not fucking work like this!” He throws his hands in the air and shakes his head and turns 360° around for the dramatic effect.

Y/N cocks an eyebrow and shrugs, “You wanted to know,”

Dean leans down then, one hand cups her face, thumb brushing over her cheek, “I know, I’m sorry, baby,” He kisses her, teeth nibbling along her lip, just a little, not even long enough but it already leaves her wanting more, “You’re making this really hard for me,” 

Chuckling, she cocks an eyebrow at him, “How hard?” 

A groan leaves his lips, “You’re a bratty little thing, ain’t you?”

She shrugs.

“One day, I’m gonna spank you raw,” Dean says as he turns around to walk back to his desk.

“Don’t promise what you can’t keep...  _ daddy _ ,” She calls after him and there’s another groan when he lets his weight help him to flop down into his chair.

  
  


*

  
  


Dean left earlier than her. Well, it wasn’t exactly early as it’s now 7.00 PM and she still has her presentation open which she is going to hold on Wednesday morning. It will be her first presentation before a bigger audience. Not really the big bosses but some who will attend are at least a level higher than her. She really wants to make it right, but also she knows that there’s no forcing it. Her head hurts from all the numbers she tries to put on the presentation and maybe Dean’s right, maybe she needs a distraction. Tomorrow will be another day. 

By 7.45 PM she reaches home. Well, the apartment looks pretty sad to be honest. She didn’t have the energy to do a lot of unpacking and there are still boxes standing around. And well, Dean said that he hated the way she left, but what he doesn’t know is that she hated it too. She just thought it was the best for both of them.

It was particularly hard to have left because it seemed like they have so much in common. It might be weird because they didn’t spend a lot of time getting to know each other and the majority of that time was spent fucking but sometimes, when it clicks, it just does and you know it. And with Dean, there was that level of familiarity when she first saw him. Something she hasn't encountered in a very long time.

Y/N takes her heels off by the door, shedding clothing on her way to the bathroom in desperate need of a shower. It’s to clean herself, but also to cool herself down. The day has been a roller coaster ride and even though Dean had a harder time to conceal his emotions, she can’t lie that it was easy for her either. She was constantly leaking throughout the day, sometimes more, sometimes less. And then there’s Dean who occasionally comes so close to her from behind and she has automatically gotten wetter from the feeling of his firm body pressed against hers. Taking off her panties in the bathroom, she takes a look at her crotch. They are truly ruined. It’s white and sticky and still damp. 

  
  
  


*

  
  
  


After the shower, she walks out with her hair still wet and a towel around her body, and even though she knows that she should leave work behind, she can’t really help but to check her phone to see if there has been an email. Maybe there’s something that she’s forgotten to do today, maybe someone is still waiting for an answer to their question. People seldom stop working once they leave the office in the financial world. Yet, it’s a world she chose to be in and she has gotten used to it.

As soon as she lights up the screen of her phone to look at it, she has to grin. There are no emails but there are texts from a number she doesn’t recognize.

Thumbing over her screen, she opens them up.

_ Oh, no. _

How did he get her number? 

Instead of being upset, though, she can’t help but grin.

> _ D: Here’s the thing, baby girl _
> 
> _ D: I want you to pack the things you need for work tomorrow and come by asap _
> 
> _ D: Don’t wear pants. Wear a skirt, no underwear _

  
  
  
  
  
  
  



	3. Three

Dean’s been nursing a boner since she walked into that damn meeting room. Even though he jumped right into the shower after he arrived home and beat one off to the image of her, it didn’t really help. It was a relief for maybe thirty minutes, but everything reminded him of her. There’s still the scent of her in his room that comes from the bedsheets which he still hasn’t changed since she spent the night here. And as soon as the scent hit his nose, he was hard again. 

It’s no fucking way to live, honestly. 

So, he did what everyone in his position would probably do, text her to get her ass over here. She doesn’t know that he pulled out her number from the scheduling they received and Dean kind of hopes that she isn’t upset about him texting her.

He felt like a teen, with a beating heart and a spinning head, and all that shit, as he types out his message. His thumb hovered over the send button. He closed his eyes, and sighed as he hit it. The damage had been done now and the only way is to keep on going so he added more texts to help it make sense.

  
  


*

  
  


It has been an hour since he sent the last message and he’s on the couch, naked, his hand lazily jerking himself off in an attempt to keep the boner alive for when she’ll come knocking. 

_ If _ she comes knocking.

He hopes she does.

Dean thumbs over his phone one-handed and gets into his messages again. She’s read them. She’s fucking read them but hasn’t answered him.

Maybe he’s an idiot for waiting. Maybe she really doesn’t want to keep this up in fear it could jeopardize her work. Maybe he’s fucking overthinking. Maybe he shouldn’t think that it can go anywhere either, at least not when they’re still competing for the same fucking position.

He chuckles when he thinks about the word  _ position _ . He wants all the positions with her, wants to get her on all fours, fuck her from behind. Wants her on top of him, below him. Wants her to spread out and moan for her daddy. 

While he thinks of all these things, his dick is leaking again. He wonders if he has to make himself come for a second time tonight or if she’ll be coming over and help him with it.

Another thirty minute passes and Dean’s ready to give up. Also, he doesn’t know if he can hold up his boner any longer without real stimulation so he gets up from the couch, thinking that maybe he should be wearing something at least because he really doubts that she’ll come. 

Dean walks past the door when he hears a knocking and suddenly, his dick twitches in interest as blood rushes to his face.

He closes his eyes and inhales, debating about putting something on because what if it’s not her? What if it’s Gabe, or worse, what if it’s the old Mrs. Osborne from across the hall who seems to always be in need of something. If it’s not some eggs, it’s flour or her sink’s leaking or her TV’s not set up right and it also seems like she’s always coming to Dean for these things.

There’s another knock as he’s probably taken too long to think about the options on what to do, and Dean decides to just risk it. It’s nothing Gabe has never seen before. They often shared the communal showers at the gym with other men too and Dean’s not shy about it. And if it’s Mrs. Osborne? Yeah, well, he bets she isn’t really unhappy to see his dick either.

Still, Dean hides behind the door when he opens it just enough to peek his head through, his face automatically starts to flush and his ears burn up when he sees her standing outside. 

Y/N is wearing a trenchcoat, some heels, and black tights. He said no underwear and somehow he wonders how high up those tights go. There’s an overnight bag around her one shoulder and a laptop bag in her hand. 

He opens the door some more and her eyes widen when she sees him totally naked with his cock throbbing and probably angry looking. 

Quickly, Dean gets a hold of her hand and pulls her into his apartment, closes the door and takes the laptop bag from her hand, the overnight bag off her shoulder and tosses them further into the apartment. 

His mouth is on hers before she can utter out a word. His hand pulls at the knot that’s holding the coat together around her waist. He breaks the kiss to take a step back to look at her now that the coat is hanging open and loose. His eyes trail down her body. She isn’t wearing a fucking bra, and she’s a good girl because she isn’t wearing any panties either, but there’s a garter belt around her hips that is holding the tights together. 

“Fucking beautiful,” Dean mumbles before he lifts her up and pushes her against the door. His mouth is quickly back on hers, kissing her bruisingly hard, his scruff rubbing against her skin, and god, he just can’t help it, hopes it won’t hurt her too much come morning.

But maybe he wants that. Wants to hurt her, just a little. Wants her to go into the office with his marks on her skin and not with only his cum inside of her.

He groans at the thought.

She’s into it too, wraps her legs around him, her arms around his neck, her fingers in his hair. Dean’s one arm is around her waist, the other one supporting her around her ass and he lets his finger skim over her ass cleft and brushes his fingertips along her puckered hole. She whines into his mouth, moans a little too when he reaches further and dips it into her pussy. 

“Fuck, so wet” Dean nibbles at her lip, “Are you wet for me?”

Their noses still touch as she nods her head.

“Words, baby,”

“Yes, for you… daddy,” She grins. It’s mischievous. It’s fucking cute.

Dean nods back, has to smirk too and he takes his hand away from her wet heat. She whines at that.

“I know baby, I got you,” He whispers low. His hand goes to his cock, positions it to her entrance and he wants to go slow, but it’s almost impossible.

With one hard thrust of his hips, Dean buries himself inside of her. He groans out loud before he latches his mouth to her throat, sucking and nibbling at her flesh, thinking about leaving a mark just there. 

“Jesus,” He fucks up to her faster, goes in deep, “Missed your sweet cunt, I promise I’ll take my time, but fuck, let daddy have this first, huh?”

There’s no answer, just nodding and her nails scratch into his back, marking him up too. Dean doesn’t care, will probably wear it with fucking pride. Wishes that people could see it. Wishes he could tell them who made them. Wishes he could tell his bosses that while she’s being a good worker for them, she’s being a good girl for him.

“Dean,” She says, and buries her face into his neck. 

He can feel her clenching. She’s probably close, and will most likely come on his fucking cock alone.

“Baby, who am I?” He asks as he pants, fucking into her deeper, changing his angle a bit to reach that button that makes her go crazy.

“Fuck,” She rolls her head back, hitting the door. Her neck is exposed and Dena dives in, sucking and licking up to her mouth.

“You’re close, I can feel it,” 

“Uh-huh,”

“Who am I?” He asks again.

“D— daddy,” Her sound is strained and her thighs around him tightens, “Fuck, I’m—,”

“That’s good, come,” He coos, “Want to feel you come on my cock, baby,”

And while he really wants her to come on his cock, Dean also has to be careful not to fucking come himself. He doesn’t want it to be over yet, although he’s sure that he most likely will be able to get it up again in no time, especially with her.

“Come,” He says again, licks a strip up her throat to her chin, “Come for me,”

“Uh-huh,” She nods, while her eyes are closed and there’s a frown of concentration on her face.

Her nails dig deeper into his flesh, carves a trail over his back as her pussy clenches around him, making him unable to move for a couple of seconds until the spasm is over.

Dean lets her come down from her high, chuckles and kisses at her cheek, spraying some more kisses all over her face, “You’re such a fucking good girl for me, baby,” He whispers, means every word because she fucking is, “Hold on,”

Y/N does. The grip around his neck gets tighter as Dean walks away from the door. He makes his way across the apartment with them still connected, but slips out of her before he lets her fall into his bed. She whines a little before she starts to giggle. Quickly, she takes off her trench coat, throws it off the bed.

“Turn around,” He instructs, “On all fours, baby,”

Scrambling around she pushes herself up on her knees, but she’s still too weak to push her body up on her elbows. Dean doesn’t mind it that much because the view is even better like this. 

She’s on his bed, the heels still attached to her feet and he takes them off, tosses them across the room. It will just be easier to manhandle her without any shoes. His hand goes to her ass cheeks, massages them before he spanks down on them, making her squeal.

“Like that, huh?” He spanks them again, because she wriggles with her ass, “You fucking love me spanking you, yeah?”

“God, yes,” She mumbles with half her face buried in his sheets. 

“Good,” His palms connects with her flesh, “Daddy likes it too,” Spanks more just to emphasize it, “Told you I would bend you over and spank you,” 

Dean spanks her twice more before he dips his face down and begins to spray kisses and lick at her ass, soothing the pain, and while he’s down there, he can’t help but bury his face in between into her cleft either. He licks a stripe along her rim, toys at her asshole, tickling her with the tip of his tongue and sucks at it. 

“Jesus,” He growls, “Even your ass is fucking tasty. Should get you a plug baby, plug you up while I fuck you. 

“Oh god,”

“Would you like that?”

“I don’t know,” 

Dean toys around her asshole with the tip of his wet index finger, dips it in just past his nail. She’s wriggling her ass at that, murmuring something incoherent while she backs up on his finger, trying to get him deeper inside. 

He has to chuckle, “Yeah, baby, you would definitely like that, fuck,” He takes the finger out and buries his face back between her ass, licks down to her pussy, and sucks at her nub. God, he can’t get enough of that sweet tang of hers. His hands are on her ass, spreading her some more so that he has better access to the source.

She wriggles her hips, pushing it back to his face, “Please,” 

“Please what, baby?” 

“Please,” She whines, “Daddy, please fuck me,”

Dean groans at the sound of her sweet begging. Fucking loves it. It goes right to his dick, making it twitch. 

“You’re a needy little thing, ain’t you?” He asks, chuckling, takes a last suck at her clit before he moves up again. He’s kneeled behind her, his one hand holding his dick while his other hand fists into her garter on the small of her back, “Oh, that’s what those things are good for, huh?” Slipping his dick in, he groans, and now he’s holding the garter in both his hand, “It’s for daddy to hold on to when he fucks you hard,”

His movements are harsh and rough as he pumps his dick into her, and judging by the soft mewls escaping her lips, she enjoys it too. 

“Reach back,” Dean commands, a little out of breath, “Pull your ass cheeks apart for me, baby,”

She does what she’s told, reaches back and rests the palms of her hands on her globes before she pulls them apart. From this angle, he can clearly see his dick moving in and out of that sweet and tight cunt. 

“That’s it,” He coos, “Just like that. Jesus, look at you, your pussy’s gripping me so tight,”

Dean lets go of her garter with one hand, sucks in his middle finger, and starts to fuck her slower. He brushes the pad of his slick finger over her asshole, feels it clench under his touch, and her pussy clenches too. He has to chuckle at that. Slowly he eases his finger into her back hole and she whimpers at the intrusion.

He goes in further, pushes down, groans when he feels his cock sliding in and out against the thin wall, “Oh my god, do you feel that, baby? Feel my finger?”

“Fuck,” She grits her teeth, “Yeah,”

“Where’s my finger?”

“In—, in my ass,” 

“That’s right,” He chuckles, “It’s in your ass, baby, you like that, don’t you? I still remember you gushing all over me last time I did that in the shower,”

“Oh god, yes,” She keens, wriggles her ass back against him enthusiastically.

Easing in another finger, he feels her getting tighter than before, and while he first had doubts and wondered if she would be able to take two of his thick fingers without much prep, his doubts have been wiped out of his mind. 

This nasty girl is going fucking crazy, moaning and keening below him, throwing her ass back and practically fucking herself on his dick and fingers. Her hands are still on her bottom, spreading it wide for Dean like the good girl she is.

He’s going to blow soon, he just fucking knows it.

“That’s it, just like that,” Dean thrusts harder, the fingers that are in her ass are pushing down, “You’re doing amazing, baby. So good for daddy,” He feels the ridges of his own cock pumping against the thin wall, enjoys it for a couple of more minutes before he pulls them out.

Y/N starts to whine at the loss, but Dean leans forward, pulls her up by her shoulder one-handed while his other one fists in her hair. He pulls at her locks, making her arch her back. His arm wraps around her body, cups her tit in his palm, fingers twirling around her nipple, pinching and pulling it while he fucks into her harshly. His mouth is licking and sucking at her neck. He’s sure he sucks hard enough to draw blood to the surface.

Dean bites into her neck too, her pussy clenches at the pain. The hand that is squeezing her tit and holding to it tight sneaks up her chest, wraps it around her throat, applies enough pressure to make her see stars. 

With a muffled cry of “Daddy,” she comes hard, an orgasm that he isn’t prepared for, and she isn’t either because her body slumps down as her sweet cunt clenched tight around him, milking his cock, making him spill warmly into her tight heat. 

He sits back on his haunches, balances her on his thighs before he lays them both down on their sides, careful not to slip out of her because the feeling of his cock engulfed by her warmth and tightness is just too good. Dean doesn’t want to slip out yet. 

Somehow, he manages to lay them down on his pillows, pulls the comforter over both of them as he sprays kisses along her shoulder and neck, his hand massaging her body. Feather-light touches skim over her skin until he rests his hand on her stomach, his thumb still drawing circles there.

Her hand comes up to cup his, guides his hand up from her stomach to her breasts, making him massage her there, too. 

“Oh my god,” She pants breathlessly. It makes him chuckle.

“Good?” He asks, lifts his head a little to kiss her cheek. 

Y/N doesn’t answer, instead, she starts to giggle. He absolutely likes the sound. 

“Can we do it again?” 

“What? Now?” 

Her hand comes up to cup the side of his face as she whips her head back towards him. There’s that mischievous smile on her face again as she nods.

Dean groans but he smirks as he plants a kiss on her nose, “I need some recuperation time. Tell you what,” He kisses her shoulder, rubs his scruff along her skin, “We eat something and then I can go again,” 

  
  
  


*

  
  
  


They order pizza and Dean gave her a shirt to wear before they step out of his bedroom, just in case Mrs. Osborne wants to come snooping. He wears his sweats but she’s still pantyless, and he likes to keep it that way. 

She’s in his lap, while they eat and she squirmed when she felt his cum leaking out. Dean felt it dripping onto his sweats too. It wasn’t disgusting. Instead, it turns him on so fucking much.

And as promised, he made her come on his tongue later in the bedroom, lapping and sucking at her sweet cunt while she fists his hair, moaning his name and the name that sounds so fucking good rolled off her tongue, “Daddy,”

They showered afterward and it was like the first night she was here. He carries her to bed and she curls against him, her arm draped over his body. 

“You finished your presentation?” She asks all of a sudden.

Dean frowns, “Baby, you really wanna talk about work now?” 

“I’m just worried,” 

He chuckles as he places a kiss on her forehead, “I finished it. If you need help with yours I can help tomorrow.”

“You’re finished? Yours isn’t in three days!”

“Yeah, I’m good like that,” He knows he sounds cocky, but that’s just really the truth. He’s an efficient worker. 

“Ugh,” 

“Why, when’s yours?”

“The day after tomorrow,”

“So, I’ll help you, okay?”

“Why would you help me, Dean?” She asks as she nuzzles closer and Dean can’t help but place another kiss on her nose.

“Because even though I like to win, I don’t like winning illegitimately.” 

“Ah,” There’s a yawn next to him.

“Yeah, now sleep, we have to be up and ready in less than six hours.”


	4. Four

As Dean had promised her, he helped her with the presentation in the morning right after they had gotten into the office.

They were running a little late since she had trouble concealing the marks he had left on her. He watched her trying to conceal it while he leaned against the doorframe, his fingers working on his tie.

He almost let it slip out that he didn’t want that, didn’t want her to conceal it, but he knew better than to be a dick.

Something clicked in him though as he watched her. Something that made his heart swell because having her at his place, having her in his apartment, in his bed, breathing the same air, being together in a confined space, all of that didn’t bother him at all. And even though they barely know each other, he still thinks he knows enough. At least it’s enough for him to think that he'd like her here permanently. There’s just this sense of familiarity that he can’t shake off even if he’d try. 

Dean knows that he shouldn’t go there. Not yet.  _ Too early _ people would say.  _ Just right _ , is what he thinks.

  
  


*

  
  
  


In the afternoon, Dean’s at his desk preparing for the next meeting while she’s still out at another meeting. They have way too many of those, if he’s being honest. However, he thinks it’s fun to rile her up. He’s seen that she took her phone with her and her laptop too, but sending things to her laptop seems to be a bit risky so he opts for her phone. 

Dean whips his dick out, gives it a couple of strokes, and it doesn’t take long for his little friend to stand erect. No wonder, he’s been horny all morning and he hopes that the execs have their answer by the end of the week because honestly, Dean doesn’t think he’d survive another week with a constant boner and impure thoughts. 

He takes a picture, making sure that the drop of precum glistens so that she can see. He sends it out to her, typing in some words for emphasis. 

> _ D: [image] _
> 
> _ D: Wish you could get out of the meeting earlier and hop on daddy’s dick _

That was a good one. Dean chuckles to himself as he places his phone back on his desk. He also now has to push his boner back into his pants and it’s really not comfortable. He doesn’t really know if he’s torturing her or torturing himself with the stunt he just pulled.

While he thought it was a good idea, somehow after more thinking, he thinks it’s the worst idea, but he can’t change it anymore now and has to probably suffer the consequences.

He doubts that she’ll answer him and thank god he’ll be gone and sitting in another meeting when hers is finished. That way he might not feel her wrath and by the time he gets out of the meeting, she maybe will have forgotten about it. 

The clock ticks and Dean has never wished for time to move faster right about now. In fifteen minutes he can go to his meeting. He even wonders if he should leave his office earlier. Go get coffee and chat to Garth who’s probably already there in the meeting anyway because he’s a fucking nerd.

Dean flinches when the door to their office opens earlier than expected. Tries to act like he doesn’t fucking know what’s going on when she closes the door and storms into the room. 

Y/N drops her laptop and her phone loudly onto her desk before she walks over to stand next to him. Dean still acts like he’s occupied, doesn’t spare her a glance.

“What the fuck, Dean!” She’s shouting and that’s when Dean tilts his head to see her standing with her hands braced on her hips. 

Oh, she’s angry, alright. But she looks absolutely cute.

“What?” He feigns innocence.

“The picture!” 

Another shout. Dean’s happy the office is soundproof. The only place sound could spill out is through the cracks of the door.

“Well,” He rolls his chair back, putting on his best cocky smirk, too. Because now the only way is forward, “Did you like it?”

“My God, Dean,” 

“Ah,” He wriggles his fingers, crooks it, and beckons her closer with it, “Who am I again?”

“You have to pull  _ that  _ card, don’t you?” She pouts and it’s then that he knows that he has won.

“Yeah,” Dean nods with a smile as he pats his thigh, “C’mon, you know you want it,” 

She licks her lips, and looks at the door.

“Nobody’s going to come in and if someone does, I can hide you under our joint desk.”

“Fine,” She exhales and walks the two feet over, she pushes her skirt up to be able to sit down more comfortably, facing away from him. 

He’s still hard and she starts to grind as his hands travel up her thigh. As his fingers graze the fabric of her panties, he feels it wet.

Dean lets out a groan, “Baby girl, you’re soaked,”

“Mmh,” She hums and lays her head against the crook of his neck. Her lips graze his skin and she starts to nibble at his flesh. Dean can’t resist that even if he wanted to.

“Did daddy do this to you, huh?”

“Uh-huh,”

“Want me to shove my fat cock into your pussy, baby? Make it a little better?” He doesn’t wait for an answer, his fingers go to his zipper, pulling out his cock that still hung out of his underwear. 

He repositions her when he has it out, slapping the hard meat against her wet pussy, making her moan, “Sit on it,”

She lifts herself up a little and pushes her panties to the side before she sits down on his cock. Dean slides in easily. She’s fucking soaked. He lets out a groan as she leans back. His hand goes to her head, tilts it so that he can kiss her sweet lips. 

“So good, baby,” He whispers against her mouth, “So fucking good for me,”

Their movements are slow, shallow, and she’s needy because he can’t reach deep enough, so she sits up straighter to take him further in. Her hands are braced on the desk, and fuck, it’s good. So fucking perfect when she bounces on his cock. 

Dean’s lost in the moment, lost in her when his phone rings. 

“Who’s it?” He asks as she is closer to his office phone. 

“Garth,” She says in between pants.

That’s the moment he realizes that he should be in a meeting and by the look at the clock, one that has already started seven fucking minutes ago. 

“Fuck,” He pushes her off him and scrambles up, pushing his wet cock back into his pants as he threads through his hair one-handed. He shoves his phone into his pocket and takes the laptop with him only realizing when he reaches the door that she’s been laughing.

That little brat.

He stalls by the door, what’s those couple of minutes going to do anyway, and looks back at her, “You did it on purpose, didn’t you? Agreeing to fuck me and make me forget my meeting?”

Y/N shrugs, “I don’t know what you’re talking about, Dean?”

“You know what? I’m almost proud of you, but tell you what. You want dirty? You can have dirty, you little brat,”

He storms out and lets the door slam close. Just for the dramatic effect.

  
  
  


*

  
  
  


Well, Dean should have seen it coming. He made his bed and now he has to lay in it. 

Halfway into the meeting, she sent him texts too. A picture of her wet cunt, two fingers deep in them. 

> _ Y/N: Daddy, my pussy needs attention _

He’s grumpy, still.

> _ D: Baby, this is the payback? _
> 
> _ Y/N: No, the fuck was the payback. Now I’m just really needy _
> 
> _ D: You are definitely something else _
> 
> _ Y/N: Find an excuse? _
> 
> _ Y/N: No one can take care of me as you do _
> 
> _ Y/N: Please? _
> 
> _ D: Baby, seriously, I can’t. They just said that we’ll stay to have a meeting with Hong Kong so I guess it’s going to be late. Can you come by tonight? _
> 
> _ Y/N: No _

Dean frowns. Well, not that she’s not allowed to say no but ugh, he would really love to spend the night with her again.

> _ D: No? _
> 
> _ Y/N: Yeah, got an early presentation, remember? Can’t be late again so I rather not sleepover at yours. _
> 
> _ D: How about I come sleep at yours? _
> 
> _ Y/N: Is my pussy worth for you to make your way across town just to sink your cock into for a couple of minutes? _
> 
> _ D: First of all, it’s not going to be just a couple of minutes, alright? Second of all, Yes. Worth all that and so much more. _
> 
> _ Y/N: Guess I’ll see you then. _
> 
> _ Y/N: [Address] _
> 
> _ Y/N: Apartment 265 _
> 
> _ D: Can’t fucking wait, baby _
> 
> _ Y/N: [image] _
> 
> _ Y/N: Me neither _

Fuck. The picture is of her spread legs with her dripping pussy and one finger up her ass. Dean bites on his bottom lip so as not to fucking groan out loud.

  
  
  


*

  
  
  


After the meeting, Dean went back home to pack some things for an overnight stay, and on his way over to her apartment, he had a flash of an idea of how to prank her. 

Y/N wants to do it the dirty way so he’s going to give her that. It’s what he promised after having been tricked into fucking her and totally missed the start of the meeting, and Dean knows an opportunity when he sees one. She’ll probably be mad. Actually, he knows that she will.

  
  


*

  
  


As soon as Dean steps through the door, she attacks him just like he did her. She kneels right down, her hands working on his belt while Dean hasn’t even had the chance to set his duffel down. She’s only in a large shirt, probably doesn’t wear anything underneath, at least that’s what Dean hopes. Clothes are way overrated with them. 

“Woah,” He whispers, “Easy tiger,”

She smiles up at him with a glint of mischief. 

Dean’s fond of that look, comes to fucking love it on her. It suits her personality. She’s the type who doesn’t settle for any less than what she deserves and strives to get the best out of life by taking what she thinks she’s earned. 

And in that moment, she thinks she deserves his cock.

He sets his duffel down, strokes the hair back on her head as he lets her pull down his zipper. Before she can pull down his underwear, though, Dean threads his fingers in her hair, one hand gripping the side of her arm to pull her up. 

His mouth is on hers, kissing her, tongue going in deep, almost making her choke. One hand squeezes her cheek when he breaks the kiss, and then he growls low, “Do you think you deserve my cock after the shit you pulled?”

“Please,” She whines.

“Yeah,” He chuckles, “Beg for it, baby girl,”

“Please, daddy, can I suck your cock?”

He pecks her lips once, “Sounds good, keep going,”

“Please, please, please,” She begs, “Please, I really want your cock, daddy,”

Dean grins, but he doesn’t let her go yet. Instead, he picks her up, carries her over to the small and round dining table, lays her on it with her head dipping off the edge. 

“You want this?” He rubs his clothed dick on her face, “Huh? Tell me how much you want my cock, baby,”

“Please, daddy,” She whines, “I want it so much,”

His hand goes to his underwear with a smile, fingers hooking into the fabric, pulling them down below his balls. His dick springs free, slaps wetly against his lower abdomen and she swallows down the drool in her mouth. 

He lays his heavy sac on her forehead, while he slaps his dick down on her face and she’s a good girl because she opens her mouths, sticks her tongue out for him to rub his shaft up and down on. 

Sex with her is by far the best he had and even though he hasn’t known her that long, he knows exactly how far he can go, knows what turns her on. 

“Look at you, baby, so eager for my cock,” He coos and he pulls her back by her armpit just a little, letting her head hang lower over the edge of the table, “You ready? Tap out anytime, okay, baby?”

Y/N nods, Yes, daddy,”

“Good girl,” Dean whispers and pushes the tip of his cock into her awaiting mouth. He slowly starts to fuck in and out of it, shallow at first, “Sucking my cock so fucking good, baby,” 

Both his hands go to her shirt, pulling it apart by the seam and there’s a sound of protest but it’s muffled by his cock in her mouth.

“I’ll get you a new shirt,” He chuckles.

Dean's hands are now playing with her exposed tits while he thrusts his dick in and out of her mouth, stopping occasionally to let her catch a breath. His hand goes further down her body at the same time his dick goes further down her throat, until he cups her pussy in his hand and starts to rub at her clit. 

She’s soaked. He fucking loves how wet she gets. Loves to bury his face in it, thinks that he should let her sit on his face, smother him with her pussy, but that’s for some other time or later or tonight, he hasn’t decided yet.

The sound of her gagging on his cock is loud in the room and Dean makes sure to pull back every time he thinks she needs a break. His fingers are now fucking into her wet cunt and she moans with her mouth full, the vibrations tickling his dick. 

He begins to fuck her harder the closer he feels he gets to his release. His hand has abandoned her cunt, but he slapped down on it, just to make her yelp up with his cock in her mouth, it’s a feeling out of this world. His hands work their way up her body again and he grabs one tit, uses it as a fucking handle to hold on to while he fucks her throat. His other hand goes to her throat, touches it, and presses down on it to feel his dick through her skin and flesh.

_ Fuck.  _

Feeling himself in her throat makes him want to come faster. 

“Where do you want daddy to come, huh?” He asks, knowing that she can’t answer, “You want me to come down your throat, baby?” 

She hums.

Dean takes that as a  _ yes _ . He comes with a deep growl, fucking into her harder, buries his dick inside as far as he can go. As he comes, his whole body trembles. She’s tapping. She’s fucking tapping and it’s because Dean still doesn’t pull back. With another growl, he pulls back, taking his dick out of her throat and it comes out sloppy with cum still attached to its tip and her tongue. 

“Jesus Christ!” He groans as he turns her around and pulls her up so that she’s kneeling on the dining table. 

He kisses her hard, rough, tastes himself in her mouth.

“Good girl,” Dean smiles against her lips, “You’re such a fucking good girl, baby. So good for me,” He strokes her hair back, sees her looking at him teary-eyed and tired, but there’s still that fucking glint in her eyes. She’s up for more already, he knows.

Fucking insatiable.

“You get your reward for being a good girl, okay?” 

“‘K,” She nods.

“I want you to sit on my face, let me take care of my girl before I can fuck you again,” Dean leaves his forehead on hers, kisses her nose softly, “Would you like that, huh?”

She doesn’t answer, but she nods with a big smile. 

“‘K,” He whispers, as he pecks her lips, “C’mon, let's get you to bed,”


	5. Five

In the morning, Dean’s in their office, touching up his own presentation for tomorrow. He steals a glance at the clock, it’s almost 8.40 AM. It’s almost time for her presentation and Y/N’s still not here. 

He wonders if he went too far.

Well, she still has about ten minutes before she has to be in the meeting room to set everything up. And if she’s not going to be here, he’ll make sure to waltz in there and bring up a sorry excuse to steal some time. He’s not a monster after all, it was just supposed to be a little prank. 

Last night, after she fell asleep, Dean manipulated her alarm, setting the alarm later than she wanted to get up. Like, not too late that she’d miss the meeting, but late enough so that she won’t have a lot of time to get herself ready. 

He set his own alarm and placed his phone under the pillow so he would wake up as soon as it started to vibrate. He did get up. Sneaked his way out of her apartment and left her there, still sound asleep.

Dean’s typing away at the email, it’s 8.47 AM now. 

Three minutes until he has to save her ass. 

That cute little sweet ass, though. 

A minute later, the door opens and she’s looking at him. Her hair’s put together but there’s no trace of makeup. She also wears glasses, god and he didn’t even know this about her but fuck, she looks super cute with her glasses. These, paired with her being angry, is really what his librarian dreams are made of.

Maybe he could ask her to role play it once. 

But yeah, maybe he could ask when she’s not mad at him anymore. 

He ignores her, stares meticulously into his screen.

Walking in, she drops her laptop bag and pulls out her laptop wordlessly.

Dean risks a glance up, sees her staring at him. Her eyes are narrow.

He smirks, “You look worse for wear. Had a rough night, sweetheart?”

“Fuck you,” She mumbles and proceeds to walk to the door.

“Well,” Dean starts, but stops because she turns around and sends him a glare.

“I hate you so much right now,”

The door closes with a bang. 

Oh well, this went super great. He doesn’t know if he should be scared that she’s so fucking mad at him or prank her some more because she’s so cute when she’s mad.

  
  
  


_________________________________________________________

  
  
  


_Oh my god_ , Y/N absolutely hates Dean fucking Winchester.

He made her late but he at least set the alarm early enough for her to be able to make it. But still... that doesn’t mean that he deserves a fucking medal, though.

The presentation went well, so at least she has that, but she’s still mad at him so if he wants to get his dick wet, he can find someone else. She’s so fucking done.

Back in the office, she is glad that Dean was out at another meeting, so at least she has a breather. 

Dean showed up thirty minutes later with a cup of coffee for her and she doesn’t know but she has a very hard time trusting it. So she looks at the coffee and up at him. 

“What?” He asks because she still hasn’t said a word, “You think I want to poison you or something?”

“I wouldn’t put it past you,” She shrugs and returns to her screen and types something on her keyboard.

“Jesus Christ, Y/N!” He growls and squats down next to her, “I’m sorry, okay? I thought a little competition is healthy. A little prank here and there. I wouldn’t do anything that would jeopardize your career in any way,”

“I almost missed my meeting,” She said drily, trying not to look at him.

“Yeah! There you have it.  _ Almost _ !”

“I don’t know what you’re trying to say, but it doesn’t make it sound any better,”

“My god,” Dean threads his hand through his hair, “You know what? I’m done apologizing,” He walks over to his own desk and sits down, “They are singing your praises. I was in the elevator with one of the execs who was at your presentation. So, even though I made you late, I didn’t make you miss it,”

“It still doesn’t make it right, Dean,”

“Whatever,” He snorts and she can tell that he’s moping. He probably feels guilty.

Maybe she’s being too harsh. He played a prank, she played a prank, and he was right, it didn’t do a lot of damage but still…

  
  
  


*

  
  
  


It was about two hours of silent treatment later that she got up to walk over to the folder cabinet in search of a folder she needed, but she couldn’t find it. The space where it should be is empty. 

Turning around, she sees that Dean’s using it. He’s probably working on the same thing as she is, which is due in the afternoon. 

Y/N sighs and goes back to her desk, deciding to work on something else until he’s finished, but after thirty minutes have passed, he’s still hogging it. 

“Jesus, are you done with the folder? It can’t be so hard to find the two numbers in there that you need, can it?”

He rolls his chair to the side to be able to look past his screen at her, “You need something, sweetheart?”

“Yeah, that damn folder! You’ve been hogging it for way too long,”

Dean cocks an eyebrow, “You want it?”

“Yeah?”

“Well, I want your pussy but that’s not something I get tonight, do I?” He chuckles, “Sometimes we don’t get what we want, baby,” Getting up from behind his desk, Dean picks up the folder and walks over to her, “You can be glad I have a conference call with England now,” He sets the folder on her desk and walks back, nodding at her as he places his headphones over his head.

He’s probably trying to make peace and ugh, it’s almost impossible for her to stay mad. Damn him and his look and the way he talks and walks. 

While Dean dials himself into the conference call, she quickly picks out the numbers she needs and returns the file back to his desk. He’s still listening in to the call but tilts his head up to smile at her. His teeth are showing white, the crinkles around his eyes are deep and god, he looks so cute with all the freckles on his face. 

Returning to her seat, she listens in as Dean speaks. He’s really good at what he’s doing, and to be honest, she doesn’t even know if she’d have a chance against him. It’s a little disheartening thinking about it. 

Y/N has to remind herself that it’s not really his fault. It wasn’t him who decided that he has to fight for a position that’s rightfully his. And he’s been helping a lot. At least, he did with the presentation she was having today. So, when it comes to him as a person, and when she puts the office rivalry aside, he is a good guy and she should definitely cut him some slack.

After finishing her report, she sees that the conference call should last another ten minutes. With a grin, she lowers herself under her desk and crawls over to where Dean’s sitting. Dean’s legs are spread and he drums on the floor with his shoe. He doesn’t know that she’s down here, but he will soon. 

Placing her hands on his thighs, she can hear him mutter something and can feel his body go stiff. 

“Yeah, I’m listening,” Dean mumbles.

With a chuckle, she skids her nails along his thighs, until she reaches his belt buckle and quickly undoes it, trying not to let it clink too loudly. Her fingers work on his button next, pulling the zipper down after. 

Her hand goes inside his pants, takes out his dick that’s still soft but it twitches in her fist and it slowly starts to grow at her touch. Dean shudders when she breathes warm air against it. 

“Jesus,” He whispers, “No, I’m sorry, just stubbed my toes,” He says above.

She has to chuckle at that and then she sticks her tongue out, licks a broad stripe from the base to his tip. Dean doesn’t make a sound, but his legs are slightly trembling. He’s probably trying to keep himself together. 

Sucking in the tip of his cock, she lets it out with an audible popping sound. The taste of him is strong in her mouth. She absolutely loves how he tastes, it makes her mouth water some more. 

The more precum is leaking out of him, the stronger his scent is and it fills her nose, clouds her mind. It’s fucking intoxicating. 

Y/N takes him in her mouth again, bobs her head up and down and tries her best not to make too much of a sound. Dean’s saying something, but she doesn’t listen. She’s so into it that her mind tunes out all the other sounds and senses. All she feels and tastes is Dean. 

With one hand she jerks him off where her mouth can’t reach in this position. With her other hand, she cradles his balls in her palms, giving them some attention and there might have been another moan. 

Humming around his girth, she gobbles him down, sucks a bit harsher at the tip before she swirls her tongue around the underside of it before she takes him in again. It seems like Dean is close because his balls are jumping in her palm and he tries to fuck up into her mouth. 

“Alright, thank you for your time, bye,” He finishes the call and she can hear how strained it sounds. 

“Fuck,” Is the next thing she hears before she feels a hand on the back of her head, holding her down on his cock while he pushes his hips up to meet her mouth. He thrusts a couple of times and then she hears the familiar growl, feels the warmth of the cum flooding her throat and mouth. 

She swallows it all down, licks at his tip and sucks at it again, making sure she catches every last drop. She cleans his shaft too, swirls her tongue around. When she finishes, she smacks her lips and Dean rolls his chair back, looks down at her.

He reaches out, his thumb caressing her cheek, before they brush over her lips, and she bites at it, making him chuckle, “Baby,” Dean’s still trying to catch his breath, “Fuck, was that to tell me you’re not mad at me anymore?”

Y/N nods.

Pulling her up by her arm, he places her into his lap and kisses her soft and gentle, “I’m glad. I could also fucking eat you up right now, but we know that’s not possible,”

“Well, you don’t know if you don’t try, right?” She grins.

“Don’t fucking tempt me. Otherwise, neither one of us will have a job by the end of the week,” He kisses her cheek before he nuzzles his face into the crook of her neck. She feels him breathing in the scent of her skin, “I’m sorry about this morning, okay? It was just a silly prank,”

“I know,” 

“Does that mean daddy can take you home tonight? Reward you for the good girl you are?”

She grins with a nod of her head.


	6. Six

The week went by so fast and the execs said that there would be another week of competition since they were both doing so well, making it hard for them to make up their minds.

Dean didn’t know right then if he should be happy or sad about it.

There were more pranks being pulled, more inappropriateness shared in their office. 

One time he woke up with her sucking him off, making him come right into her throat and he rewarded her with letting her sit on his face. He absolutely loved to be smothered by her pussy. He also totally forgot about the time or what day it was so he turned up late to his meeting only because he wanted to give her more orgasm than the last time he let her mount his face.

He once fingered her right in a meeting, had her gush and come around his fingers and when everyone was making an exit, she had to stay back and clean her chair. Dean couldn’t stop laughing once she got back into the office, which earned him another round of the silent treatment for the rest of the work day. 

The next day, she did the same to him, rubbed over his clothed dick so good that she made him cum right in his pants while Garth was babbling about fucking stock markets. Dean had to go home to fucking change his pants and since then, he took some more pants and underwear with him, stashed them in his desk drawer in case of emergencies like these.

Y/N had spent the weekend with him, though. So there’s that. And they didn’t just fuck and that’s progress. They went on walks, went out for dinner, did some shopping for naughty things and he really bought her a butt plug. She said that she wants to try it, but he shouldn’t push her. He didn’t. Instead, he let her take it home but he asked her if she could send him a picture when she uses it. She just laughed it off, even though he wasn’t even joking and was dead serious about it.

Spending time with her felt good. It was familiar, it was like he had known her for so long already and not just a little more than a week. And the sex,  _ Jesus _ , the sex was incredible. But aside of that fucking mindblowing sex, he really enjoyed her company. 

  
  


*

  
  


The working week after their weekend together started just like the previous one ended. With some office rivalry to warm up. 

Monday, she brought him coffee and poured salt in it. Dean spat it out all over his screen and keyboard, and it was ten minutes after that he finished, she finally stopped giggling like a goddamn idiot.

They still tried to keep the other one from showing up for work on time, but it didn’t really end well, and on Wednesday, they were both late. 

Somehow, Dean really hoped that it’ll be over and done with by the end of the week because he doesn’t think that he can keep this up any longer. 

It’s now Thursday and he’s fucking exhausted by the tension, but it’s also now that he realizes something.

He came back from a lunch meeting to see her standing by the shelf, holding a binder in her hand and reading through it. He doesn’t know what it is but he’s mesmerized by the level of her concentration and she’s wearing her glasses and absolutely looks like a naughty librarian with her pencil skirt and high heels. Definitely looks delicious enough to be devoured.

And Dean can’t stop himself from standing behind her, pressing his body to her backside, feeling her soft and warm in front of him. His dick grows uncomfortably fast, swells up with lust and the rest of the blood goes to his heart as it starts to pump faster.

He dips his face down, nuzzles his nose along her neck. It’s like the first night they met. His hand skims along her body down to her thighs and she fucking lets him, like the good girl she is. 

“Dean,” She says, “We shouldn’t,” 

“Why?” He mumbles against her skin, “You look so good, baby, want you so bad,”

It’s the truth. He’s so hard he could pound nails and she hasn’t done anything yet. He’s whipped. Dean knows that too.

“Because I don’t think you can be quiet,” She pushes the binder back onto the shelf and turns around. Her hands play with his tie, wraps it around in her hand to pull him down for a kiss.

“Why?” He asks again, breathing hot air against her lips and she chuckles. 

It wouldn’t be the first time they fuck in the office and he’s been holding himself up pretty good when they do it.

“Because of this,” Her hands leave his chest to skim down the side of her body. She turns back to face the shelf and lifts up her skirt past her round ass. 

And then he sees it and it’s like someone had punched the air out of his lungs. Dean’s not able to breathe right.  _ Jesus _ , even his cock starts to twitch violently at the sight. She bends forward and spreads her ass with her hands, granting him a better view and possible access.

“Fucking hell, baby,” He mumbles, still can’t believe what he’s seeing. There’s a black diamond looking out of her asshole. She has used the butt plug he bought her. Dean swallows, “How long have you been wearing it?”

Y/N shrugs, “Since this morning,”

“My fucking god, Y/N, fuck,” 

“You like it?”

“Like it?” He asks and he runs over to the door, locks it just to be fucking safe. When Dean’s back behind her, he gets down on his knees, using his hands to help her keep her ass spread as he dives into her cunt, licking and sucking at it. She hasn’t worn any panties, and has stopped wearing them to work for a couple of days now because she said that there’s no point if she’s going to ruin them every day anyway.

He trails his tongue back over her rim to her ass, the tip of his tongue tickles around the plug and she moans as she presses her body closer against the shelf.

“I fucking love it. That’s fucking beautiful, baby,” Dean coos, and he pulls at the plug just a little, sees her asshole widening before he pushes it in only to repeat it again. God, he could just spend his day doing this because it also elicits the sweetest fucking moans out of her, “You did that for me, huh?”

“Only for you, daddy,” She says sweetly, almost too sweet. His heart aches as much as his cock.

Dean's hands leave her ass to open up his belt and feels relief when he pulls down his zipper and releases his throbbing dick. He spits into his palm, jerks himself off to the sight in front of him. He bites into that ass too, can’t stop himself from doing it and she lets out a squeal, accompanied by a chuckle.

“Baby girl, I wanna fuck you bad, and I know that we should probably move this to the bed but fuck, I need a taste,” He jerks himself faster, is already leaking profoundly, “Can I, please?”

He looks up to see her nodding and Dean stands back up, leans over to her to kiss her properly. His tongue goes in deep, swirls around her own tongue in her mouth. 

“I’ll be gentle,” He promises and there’s another nod of approval, “Spread your cheeks for me, baby,”

Her hand goes back to her ass, grips at her flesh and spreads it out for him. He groans at the sight and tries to hold himself together, tries not to lose himself before he even gets to be inside.

Dean spits into his hand, slathers his cock with his own spit before he guides the tip to her pussy, letting the head catch the rim and pushes in just a little. 

“Fuck,” He groans, “It’s already so fucking tight,”

His hand goes to her head, making her tilt it to the side and he leans forward as he pushes in further, watching the reaction on her face before he presses a kiss on her temple and along her cheek. 

“So good, baby, such a good girl for me,” He whispers low and has to stall when he bottoms out, “You feel fucking amazing. You were tight before, but fuck!” He moves out of her slowly, moves in again, “How does it feel for you? Are you okay?”

“God,” Y/N breathes out, “Full, feels so full… but it feels good,”

Dean chuckles as he noses along her temple, “That’s good, want it to be good for you too,” He whispers as he moves in and out of her unbearably tight cunt in a slow pace.

“Daddy?”

“Huh? What’s wrong, baby?”

“Can you fuck me harder and faster?” She arches her back for emphasis, drives her ass against his dick, making him go in deeper than before.

“Jesus Christ,” Dean growls, “I don’t know if I can last long if I fuck you harder, baby,”

“Please? For me? You can fuck me again later, but I want it hard now, daddy,”

“Goddammit,” Dean grits his teeth and he pushes his body away from her, smacks her ass before he digs his fingers into her hips and begins to fuck her harder, “You know I can’t say no to you, right? You fucking know it and you always use it to your advantage,” He pants and keeps fucking her hard, “Gonna spread you out tonight, baby, spank you for thinking that you’ll always get your way,”

He can feel her pussy clenching at the mention of the spanking. She is definitely something else and Dean would be damned if he’d let her go.

“You love it when I’m bratty,”

“Damn right, I do,” 

Yeah, he does. Very much. 

He spanks down on her ass again, making her yelp up and then he feels it, the tight squeeze, the wetness that surrounds his cock. She just fucking came from his cock and the buttplug alone. It’s the best fucking thing.

With a groan, Dean comes too. It’s impossible to hold out longer, not when her pussy’s so fucking tight. He might try that ass tonight if she’ll let him. His hands are on her ass, kneading it as he comes down from his high. 

Dean chuckles when he pulls out of her and Y/N lets out a soft whine. His dick comes out with a blotch of his cum. They will need to clean the floor. Again. It’s not the first time.

He quickly walks over to his desk and pulls out tissues from the drawer, walks back with them to clean her up and himself before he cleans the cum from the floor. Dean places a kiss on each of her ass cheeks and one square on that black diamond head of the butt plug before he pulls her skirt back over her ass where it belongs. 

When he tucks himself back too, he grabs her by the waist and turns her around, kisses her soft and long, “I have to be somewhere but you’ve gotta wait for me before you go home, okay?”

“‘K,” She says and Dean leaves a kiss on her forehead before he makes his way out.

  
  
  


_________________________________________________________

  
  
  


Dean’s been gone for a long time, and it’s already past 6.00 PM. She’s finished with her task for today and is sitting at her desk, trying to sort emails and go over the tasks for tomorrow just to occupy her time. He said she should wait, but he’s taking so long.

After he left she had already opened the windows to get the sex stink out. She has also gone to the bathroom and cleaned herself thoroughly down there and pulled out her panties from her drawer, and even wears a pad. She hates to soil her skirt with his cum when she’s not wearing underwear

It’s 6.34 PM when Dean comes back. 

“Uh,” He says, with his hands in his pockets, and he looks somber. Clearly, something’s wrong, “They are expecting you in the boardroom.”

“What?” She frowns, “Why?”

“I don’t know,” Dean shrugs as he walks back behind his desk, “I wouldn’t keep them waiting,”

“Okay?” Her heart starts to race and she wants to ask Dean more, but apparently, she’s wanted now and it seems to be important so she gets up, and before she closes the door, she sends him a glance, Dean nods with only the smallest of a smirk on his face.

The offices are mostly empty at this time of the night. Occasionally people would stay longer, but the majority already went home. Her heels click against the stone floor and her heart almost jumps out of her chest the closer to the boardroom she gets. 

Mrs. Mills and Mr. Turner are already waiting. 

“Please, take a seat,” Mrs. Mills says and points to the chair. 

She takes a seat and notices that the chair’s still warm. Dean must have been in here. She can still smell the traces of his cologne. What just happened? Did he rat her out? Will they tell her now that he got the job and not her?

“Miss Y/L/N, let’s cut to the chase because we all would like to go home now. The reason we asked you to come in here is that we would like to offer you the job.”

Her eyes widen.

“I- uh, really?”

“Yeah, congratulations,” Mr. Turner chimes in, “You’ve done remarkably well for someone who just started two weeks ago. You were determined, you did your research well and you always had good arguments to prove your point. We are sure that you’ll be a great addition to the partner team.”

“Wow,” She huffs out, “But what about Mr. Winchester?”

“He was actually the one who told us to choose you and brought good points to the table,” It was Mrs. Mills who spoke, “He’ll be keeping his job, but you’ll move into your new office on Monday. We’ll get the contract on your desk by tomorrow,”

Dean did what?

Why?

Oh my god. And then it dawns on her. She got the job! She really got the job! 

“Okay, thank you so much,”

“It’s our pleasure,” Mrs. Mills stands up from her seat and she does too. The two of them shake her hand before they disappear and she waits until they are gone but she’s too giddy and barely can contain herself. 

When both of them were out of earshot, she runs towards the office she shares with Dean, hopes so fucking much that he’s still here. 

Y/N’s out of breath when she opens the door. Dean looks up from his screen, but he knows because he’s grinning. He rolls his chair back, beckons her over with a hand gesture. 

And she goes in willingly, takes off her shoes and sits into his lap, curls herself against his body as he holds her. 

She feels safe with his arms wrapped around her. And as independent and strong as she may be, she enjoys that he’s taking care of her. Absolutely loves how he cares beyond the incredible sex they have.

“Why?”

“What?” Dean asks. The bass of his voice rumbles in his chest.

“Why did you tell them to choose me? They would have chosen you.”

He chuckles, “I don’t think they would have. You’re clearly the better candidate. You’ve shown that you can do anything when you set your mind to it and even though you didn’t know the company, you still did better than me,”

“Why did you give up the promotion? You didn’t want it?” She nuzzles her face into the crook of his neck, smelling the scent she’s grown to love. 

“Not really, to be honest. My brother is moving into the city soon. We are going to try and open our own business one day so it isn’t bad if I have some money on the side until our business takes off. So, you know, I wanted the job, at least a part of me wanted it,” He pauses to place a kiss on her forehead, “But then I realized that I shouldn’t risk what I want most for something I want now,” 

Pulling her head back she looks at him, sees him smiling. 

“What do you want most?” She asks with a beating heart because she thinks she knows. She would just love to hear him say it.

“You,” He says, pulls her close by the back of her neck. He kisses her soft and gentle, “I want you so much,”

She can’t say she doesn’t want him either, because she does. So fucking much.


End file.
